Take Care with Josh Ramsey · 2025-05-13 · 16 min
Key moments - from our scoring
Substance score
50 / 100
Five dimensions, 20 points each
Josh Ramsey's journey into hospitality reveals a tension between corporate efficiency and human connection that defines modern leadership challenges. Starting with a theology degree and pastoral background, Ramsey joined Hilton's revenue management team after earning an MBA in finance and entrepreneurship from Southern Methodist University, where he was inspired by Conrad Hilton's philosophy of spreading hospitality's warmth and promoting world peace through travel. However, he quickly discovered that corporate culture often contradicts stated missions - the gray cubicles and siloed work of Hilton's revenue management center felt disconnected from the human-centered vision he'd learned. Rather than leave, Ramsey applied his pastoral instincts, organizing team connections and eventually partnering with Chris to build a new business unit serving Hampton Inns, scaling from 30 to 1500 hotels while hiring 300 people. At Prosper Hotels, Ramsey and his partner embedded care as their foundational business priority, using Maslow's hierarchy framework. He argues that leaders avoid mission drift by remaining integrated within their organizations (not separating from them), understanding their own values deeply, and creating space for human friction and connection rather than frictionless automation. The conversation emphasizes that self-care and self-love form the bedrock of authentic leadership capable of caring for teams and guests alike.
After earning an undergraduate degree in theology and deciding against becoming a pastor, Ramsey pursued an MBA in finance and entrepreneurship at Southern Methodist University, where Hilton recruited him into their revenue management team at their corporate center.
His experience at Hilton's revenue management center - where corporate culture contradicted Conrad Hilton's humanistic mission - drove him to apply his pastoral background to leadership, and he and partner Chris built Prosper with employee care as the foundational business priority using Maslow's hierarchy.
He argues that leaders must love themselves unconditionally, as a parent loves a child, before they can authentically care for their teams and guests; anything less than this integration of personal values gets detected as inauthentic by employees.
General managers managing pricing, occupancy, and future business strategy constantly experience stress that prevents them from being present with guests and teams; Prosper's solution is to relieve that stress so GMs can focus on hospitality and human connection.
He believes humans need genuine connection, to be seen and heard, and to feel belonging; frictionless automated experiences like McDonald's miss the point that hospitality is fundamentally about real human-to-human engagement.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode contains some meaningful ideas about leadership philosophy, self-care as foundational to team care, and the tension between frictionless scaling and human connection. However, much of the content is motivational reflection rather than novel, actionable insights. The Maslow's hierarchy of business priorities, the Jerry Colonna question about complicity, and the Archimedes lever metaphor are interesting but not deeply explored with specificity or evidence.
We've got to make sure that the fundamental element as we build this business is that we take care of people, that we take care of each other. And that is our Maslow's hierarchy at Prosper of our business priorities and that's the foundational layer of our pyramid is to take care of each other.
how are you complicit in creating the conditions you say you don't want?
The core framework - that leaders must model vulnerability, that self-care enables team care, that scaling must not sacrifice culture - is thoughtful but represents widely circulated wisdom in leadership circles. The Conrad Hilton references and Mr. Rogers letter are borrowed inspirations rather than original thinking. There is little contrarian or first-principles argumentation; mostly affirmation of existing values-driven leadership philosophy.
Conrad Hilton, he has like a, He has a saying of to achieve big things, you must dream big dreams
I'm proud of you. And it's an editorial writer that built a relationship with Mr. Rogers.
Josh Ramsey is a managing partner at Prosper Hotels with 20+ years in hospitality, including significant tenure at Hilton where he scaled a revenue management business from 30 to 1500 hotels. He has direct operational experience and genuine skin in the game as a founder. However, the interview format and focus on personal philosophy rather than business specifics means the guest's practical expertise is underutilized.
Josh Ramsey one of the managing partners in At Prosper hotels, revenue management, and he's got a long history in the hospitality industry, working for large brands like Hilton. He's got over 20 years of experience
we started with 30 hotels and ended with 1500. We started with no people and hired about 300 people in the process of, I think, five years.
The episode lacks concrete data, metrics, or examples to substantiate claims. The 30-to-1500 hotel scaling story includes timeline and headcount but no revenue, margin, retention, or customer impact data. Most insights are framed philosophically rather than empirically. No specific client wins, problems solved, or measurable outcomes are discussed beyond the hiring number.
we started with 30 hotels and ended with 1500. We started with no people and hired about 300 people in the process of, I think, five years.
how do we take care of the people in front of you that are checking in. You've also got all of this stuff behind the scenes to manage
KC Procter asks respectful opening questions but rarely pushes back, challenges claims, or pursues specificity. The interview reads as a values affirmation rather than an investigation. There are no moments where the host contests assumptions, asks for concrete examples, or explores the gap between espoused values and operating reality. The conversation is warm but lacks edge.
but Josh, I don't know. Anything, really anything about your origin story in hospitality? So I'm curious, like, how did you get started?
I'm curious, as you and your partner, Chris are leading your own company now, your own culture,, how can leaders. Avoid the pitfall of veering away from their core values
Computed from the transcript - who did the talking, and the words that came up most.
In the inaugural episode of Take Care, Josh Ramsey explores the foundational principles of authentic hospitality. Josh shares his unconventional journey into hospitality, inspired by his upbringing rooted in service and a surprising connection to Conrad Hilton's vision. He recounts his early experiences at Hilton and the pivotal moment he realized the importance of fostering a caring and connected work environment. Josh also discusses how his personal values of care and "otherness" shape his leadership philosophy at Prosper , where taking care of their team is the cornerstone of their success. Josh offers profound insights into creating a culture of trust, vulnerability, and unconditional appreciation for individuals, drawing inspiration from the wisdom of Mr. Rogers. This episode lays the groundwork for understanding how exceptional hospitality truly begins from within. Follow Josh Ramsey on LinkedIn
Transcribed and scored by The B2B Podcast Index.
Welcome to Take Care, a podcast exploring the heart of hospitality. In each episode, we'll uncover how authentic care creates meaningful connections that transform service. We'll talk with industry leaders about the interconnected circle of hospitality, how caring for ourselves enables us to care for our teams, who then deliver exceptional experiences for our guests. Take care because exceptional hospitality starts from within.
KC Procter: All right, folks today. We are interviewing Josh Ramsey one of the managing partners in At Prosper hotels, revenue management, and he's got a long history in the hospitality industry, working for large brands like Hilton. He's got over 20 years of experience, and he's just got a really big heart for the overlap between leadership and hospitality and taking care of people, both guests and hospitality teams. but Josh, I don't know.
Anything, really anything about your origin story in hospitality? So I'm curious, like, how did you get started? Josh Ramsey: Yeah okay I would say it's probably starts with my parents cause my dad was a pastor and my mom was a teacher. And so like I grew up in this life of we were part of the community and very much serving the people around us.
I went to school to become a pastor. So my undergrad is in theology. And then I decided that wasn't the profession, I think, that I was to be in and figured that out when I was. a senior about to graduate.
so , that led me a bit on a meandering path, but I did, I ended up at , Southern Methodist University to get my MBA. And so I was studying finance and entrepreneurship there. And I just happened into, Hilton was recruiting MBA grads from, and had posted like to SMU and happened into the revenue management team at Hilton from that. So I was managing a bank and then got that job at Hilton.
And So that's how I like got into it. The, where it, where I would say, it gets interesting is once I got there, I was really excited. Like I got fired up about this idea of so Hilton. Started from this, unique character, right?
Conrad Hilton. And I've I've got an old copy of his book right here. It's called Be My Guest. A few points I remember from orientation that first day was like, Conrad Hilton, he has like a, He has a saying of to achieve big things, you must dream big dreams I loved that line.
This is part of the, the Hilton vision statement is to spread the light and warmth of hospitality. And I loved that idea. then one more that wasn't, I don't think was like part of the mission statement, but something that I found that Conrad Hilton said was that he wanted to promote world peace through travel. And so all of that stuff, like really stuck with me.
I was like, this guy, is onto something. I didn't know that I needed it, but I got like very into it. So this, I thought this is like the last, the very last chapter in this very, dense book which just says there is an art to living. So it's like his last chapter is just I think a charge to people like, there's a good way to live your life.
But like this resonates with me. The only thing we are absolutely sure about the common denominator is that within each is that divine spark called life that each was born in the image and likeness of God. of God. As we strive to know more about people, to understand rather than to be understood, we are in a better position to fulfill the commandment to love our neighbor as ourselves.
And I thought that was like, so good and so forward thinking, inclusive, like empathetic. And it, yeah it like, strikes a chord with me. KC Procter: Absolutely. That'll preach.
Josh Ramsey: Yeah. And so , I was lit up about that. And then I went downstairs from like orientation to like my cubicle, and it was a different life. Everyone was heads down, everyone was to some extent like, To each their own and every man and woman for themselves, and I don't know, I've, it was the first time that I was in this kind of like corporate life that I, and I didn't, it didn't, it was, gray walls, gray cubicles, and I didn't like it.
I was like, I had a really hard time with that. I didn't want to stick around. Actually. I was like, okay, this is not, this isn't what I want to do.
And, but at some point I I was like, okay, what was this guy up to, and like, how can I help? bring that to what's going on in this office. It was it was a center like for revenue managers. And there were a lot of great people there.
Don't get me wrong. I love so many I'm still connected with many of them. There was, I think probably a hundred something people, but it was just like the environment itself made it hard to like, Be helpful. And so I was like I'm going to like, start just putting my, pastoral hat on I'll KC Procter: Sure.
Josh Ramsey: to the whole office. I'll get everybody to go to happy hours. I'll try to some Things and get these folks together and get them to laugh and have a good time and find what they have in common. And.
Just start connecting people. And that started to turn things around. I was just, a manager there at, but the senior director that was in charge was like, Hey, this guy is he's he writes good emails. So I'm going to have him start writing all the emails for, Like the broader communications.
And then I got to be on a project with my now partner, Chris, at Prosper, where we built were able to build a new business within that revenue management center to focus on these smaller Hampton Inns, the smaller hotels. And Chris and I were able to grow that together from we started with 30 hotels and ended with 1500. We started with no people and hired about 300 people in the process of, I think, five years. , but when Chris and I started that, we were like, We've got to make sure that the fundamental element as we build this business is that we take care of people, that we take care of each And that is our, we have a Maslow's hierarchy at Prosper of our business priorities and that's the foundational.
layer of our pyramid is to take care of each other. and that means so many different things. But it's very much about having this underlying element of trust. and care for ourselves and for one another.
And that's how I got, started at hospitality? KC Procter: , I love that. I'm curious, as you and your partner, Chris are leading your own company now, your own culture,, how can leaders. Avoid the pitfall of veering away from their core values or from that, from their mission.
Josh Ramsey: I think of a couple of things, is leverage and one is otherness. And so I'll start with the otherness managing a company, I think about it in parenting when I first became a parent, I thought that the job was like, how do I set up the right rules and manage these small people, how do I effectively control these small people? And then I realized that doesn't work, this idea of probably separateness of, how Where I'm thinking like, why is my kid not doing what they're supposed to?
Looking at the larger, the broader environment, and I'm not like paying attention to this. This organism exists within its environment, and there's a lot that goes into that. And a lot of it points back to you as the parent, or you as the leader, of maybe maybe you're anxious about this, and that's why your kid is acting up, right? Or what are you doing?
Jerry Colonna. He said how are you complicit in creating the conditions you say you don't want? I love that line. And I think about that, what you're saying about how do you carry a vision as you grow it's important that you don't ever separate yourself from organism, that you're still part of the organism.
What's going on and fully part of that ecosystem. , because the further you get disconnected the easier it is for things to, go on their own somewhere else, not accomplished than what you maybe set out to do. I think that there is supposed to be some friction in the system, right? I think about great, restaurant experiences I've had.
There is, Some engagement with that, server and chef and kitchen, like you want there to be a bit of like real human to human connection. It's not just about, like you're saying with McDonald's, like you could provide this like seamless frictionless. consistent experience, but I think for us as humans, we want connection. We want to be seen.
We want to feel heard. We want to have a sense of belonging. And before you even have those three, you want to know that you're safe, and , that all goes into care and hospitality as well. Archimedes lever , where he says, give me a lever.
Long enough and a place to stand and I can move the world. And I think that we currently live in this world where so many people have super long levers and they're just moving things with less effort. but, and making substantial changes, right? And so as people think about, okay, how do I scale this company?
They borrow more money, they grow fast, they hire more people. They, stack on AI, there's all of these things that are happening to accomplish maybe what they say is the end goal. But a lot of times. Miss the point, and so for us we keep coming back to the whole reason we started this company is One to take care of each other and have jobs that we like and that we want to work at and do together Two it's to solve a problem, which is really Helping these hotel teams in general have the folks that work there have a lot going on, so much is expected of them.
You've got to take care of the people in front of you that are checking in. You've also got all of this stuff behind the scenes to manage to make sure that experience is going well. And then for every date in the future, you're trying to manage the situations that are That you're trying to handle, right? What business should I take in for next week or next month or next quarter?
What should my strategy be to fill this hotel with the most profitable mix of business, right? Those are things that if a GM is like constantly worried about that, they can't be present with the guests and with their team. And so for us, that's the root of what we're trying to do is how do we take care of. How do I get that off of, the general manager's mind?
Can I relieve that stress so that they can then take care of their team and the guest? And for me, I think as a leader of an organization, no matter how big or small, what we were talking about of me taking the Conrad vision and trying to live that out, you've got to have your own personal values that you're trying to live out, that are aligned with who you are, because anything that's not that people see straight through it. I think, people talk about integrity like it's just being honest and consistent, but I think it's about being integrated that you fully have this truth embodied in everything that you are, right?
You know what you're about and you work to accomplish those things.\ And so the more you know yourself and the more you love yourself thinking about the way that you love your kids your own children with an unconditional love, how can you love yourself with that same kind of patience and unconditional love, understanding, gratitude for their quirks, there, , I think about the way that like, sometimes I talk to myself or the way that maybe I used to talk or think about myself.
is not the same kind of love that a father has for his children, I think it's super important that taking care of yourself and loving yourself. Is a fundamental layer of the part of that taking care of others. This is a book I, I found eye opening and encouraging for me when I found it, , I'm proud of you. And it's an editorial writer that built a relationship with Mr.
Rogers. So this is just an email that Mr. Rogers sent to this guy, Tim. and it's just it's a quote.
He said, Fred shared with me the following Arabian proverb, a friend is one to whom one may pour out all the contents of one's heart, chaff and grain together, Knowing that the gentlest of hands will take and sift it. Keep what is worth keeping, and with a breath of kindness, blow the rest away. then Fred said, I thought of you when I read the above. I'm proud of you.
And I I think maybe that's also part of one of my values and what I've found depth and meaning in life Is the depth of friendship that I have . I have maybe three friends that I'm very close with but this beauty of being able to be fully myself and fully vulnerable and still know that I'm loved. And to not feel like I have to do anything or be anyone to get their approval. And so that's part of also for me, what it means to take care of other people I want to see them for who they are value and appreciate them just as they are, and be proud of them and who they are right now, not needing to do or be anyone else than they, who they are right now, right?
I feel like I have lived so much of my life feeling lesser than or just not enough. it's just this sense that was always inside of me that, not enough, , not good enough, not smart enough, not strong enough, fast enough. You name it. and feeling now fully.
Rooted, standing firm in who I am, and part of that's because I've been taken care of by other people, other people have held me up when I didn't, have enough strength to do that. KC Procter: I love that. That's beautiful. Josh Ramsey: thanks.
KC Procter: Thank you so much, Josh. Appreciate your time. This was fantastic.
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